On Culture: Rigor with Room for Play

Myste Wylde
7 days ago
6 min read

“Play is the exultation of the possible.” - Martin Buber

Dear Culturati Insider,

Possibility feels tight right now. We're stuck in a state of cautious pessimism. Markets are under pressure and trust is thin. Under strain, many leaders default to seriousness, speed, and control, the familiar assumption that gravity equals rigor. However, the leaders expanding what feels possible are doing something much more effective. They're leaving room for purposeful play.

Play creates psychological safety, allowing ideas to surface before decisions harden. It invites ideation and experimentation and reframes failure as learning. Research shows this directly reduces burnout while increasing creativity and adaptability, at a moment when nearly four out of five workers report chronic stress.

The stakes continue to rise. At Davos this week, trust resurfaced as a material business risk, with new data showing 70% of people retreating into more insular worldviews. In contrast, leaders in developing markets earn higher trust by staying close to their people, explaining trade-offs plainly, and treating emotional intelligence as part of the job.

Leadership style matters here. Leaders who communicate in ways that fit who they are, use humor to release tension, and prepare with intention create clarity without force. Founder, Wes Kao, shows how small habits like a 30-second pre-brief significantly improve outcomes. And author, Chris Duffy, shows how laughter and visible humanity increase trust and ease collaboration under pressure.

Underlying this is a more insidious challenge. Data continues to show a gap between results and conduct. Short-term wins often reward coercive behaviors like pressure, fear, and control, while genuinely positive traits such as transparency, empathy, and authenticity lose effectiveness when applied without judgment or context. When leaders over-index on any single strength, even a good one, decision quality can suffer. (Think transparency that turns into oversharing during uncertainty, or empathy that avoids hard calls and leaves teams unclear about direction.) That risk deepens with a widening self-awareness gap, where most leaders believe they see themselves clearly and few actually do. Purposeful play helps close that by keeping feedback active, surfacing blind spots early, and creating space for curiosity, reflection, and course correction before trust breaks down.

With room to play,

Myste Wylde, COO

Why Leaders Need to Take Play Seriously

INSEAD Knowledge

By Manfred F. R. Kets de Vries

Summary: Play belongs at the center of serious work. Research shows playful elements reduce exhaustion and cynicism while increasing innovation, and with nearly 79% of workers reporting chronic stress, its absence poses real performance and health risk. Studies of hundreds of employees and students link play to lower stress, higher creativity, and stronger resilience, qualities leaders expect yet often restrain through rigid systems. Cultures that optimize only for efficiency drain energy and insight, while those that normalize curiosity and iteration build endurance, adaptability, and sustained innovation. Play creates psychological safety, encourages experimentation, and turns failure into learning, expanding judgment and problem-solving capacity while supporting a sustainable workforce.

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The Other PMF: Wes Kao’s Framework for Founders Who Want to Communicate — and Lead — Better

First Round Review

By Wes Kao

Summary: Wes Kao, co-founder of Maven and the altMBA, introduces “personality-message fit,” a practical framework for founders who want their communication to land with clarity and authority. Her argument is simple and operational: effective leaders align how they speak with who they actually are, rather than borrowing styles that feel forced. Through coaching examples, she shows that awareness of personal baseline, energy patterns, and communication strengths allows leaders to adjust delivery using clear levers such as framing, word choice, and structure. Small habits like a 30-second pre-brief before conversations materially improve outcomes by anchoring messages to audience needs and desired decisions. Kao emphasizes experimentation, real-time observation, and precise feedback decoding to refine impact, while encouraging founders to own their distinctive point of view. The result is clearer thinking, faster alignment, and communication that builds trust without dilution or performative polish.

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5 Reasons Why You Should Laugh More and Not Take Yourself So Seriously

Fast Company

By Next Big Idea Club

Summary: Chris Duffy, a comedian, television writer, and host of TED’s award-winning How to Be a Better Human podcast, shares five insights from his new book Humor Me: How Laughing More Can Make You Present, Creative, Connected, and Happy. His central point: humor is a practical advantage, because paying attention to everyday absurdities makes people more relatable, more curious, and easier to work with. He highlights research showing that high performers become even more liked and trusted when they show small imperfections, like spilling coffee, because competence paired with humanity builds credibility. Across the five insights, laughter supports presence, fuels creativity, strengthens connection, and lowers tension, which improves collaboration and decision quality under pressure.

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Why Dark-Side Leadership Persists And Bright-Side Leadership Fails

Forbes

By Mary Crossan

Summary: Leadership research shows a recurring disconnect between results and conduct: fear-based or coercive leaders often post quick wins, while inspiration-driven leaders can stall when positive traits are applied without calibration. The underlying issue is how effectiveness gets defined and rewarded. Even with ESG metrics or balanced scorecards, most decisions still revert to shareholder returns and short time horizons, allowing damaging behavior to slide when numbers look strong. Two factors matter most: leader character, rooted in sound judgment, and context integrity, the norms that reinforce disciplined behavior. Weak contexts reward dark-side leadership; strong contexts allow bright-side leadership to scale. Problems intensify when single virtues, such as authenticity, run unchecked, compounded by a self-awareness gap where roughly 90% of leaders believe they are self-aware and only 10–15% demonstrate it in practice.

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What Leaders Can Learn from Developing Countries About Rebuilding Trust

World Economic Forum

By Nick Studer, John Romeo, Ana Kreacic

Summary: Trust has shifted from a cultural concern to a material business risk, a point underscored this week in Davos as new data showed 70% of people retreating into more insular mindsets. Against that backdrop, global workforce data offers a clear counterexample and a practical path forward. Employees in developing markets report significantly higher confidence in senior leaders at 67% versus 52% in developed economies, driven by clearer communication, closer proximity to leadership, and a belief that decisions serve the whole workforce rather than a narrow few. Leaders in these contexts modernize outdated leadership models, explain trade-offs plainly, treat emotional intelligence as a performance requirement, and stay visibly connected to the frontline. As organizations span five generations and AI accelerates complexity, trust emerges as a daily operating discipline built through clarity, proximity, and follow-through, not left to messaging, slogans, or charisma.

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Join us on Friday, January 30 from 1:00–2:00 p.m. CT for our next Culturati: LIVE, where we’ll explore how AI is reshaping work by shifting advantage from tools to judgment—what leaders automate, what they intentionally protect as human, and how clearly those choices are communicated. Drawing on new research from Cro Metrics, Gwen Hammes will examine the growing divide between tasks people readily delegate to AI and moments where human discernment, creativity, and trust remain essential, and what this means for operating models, workforce design, and culture. In conversation with Al Dea, the session will unpack how executive teams are rethinking decisions, roles, incentives, and trust signals as AI scales—highlighting the renewed value of human-verified work, in-person and relational experiences, and the ways predictive systems are beginning to shape priorities—offering a clear view of what’s likely by the end of 2026 and the leadership choices that can align pace, people, and principles without losing coherence or credibility.